Lenny's Podcast: Product | Career | Growth
00:39:26 · Lenny Rachitsky, Jenny Wen
[00:39:26] S1: And do you see yourself going back into management long-term? [00:39:28] S0: I will. I probably will. I think I really just love helping a team build the best product possible. And my motto there is, whatever it takes. If it's somebody that, if the team needs somebody to give the team direction and set up the team and whatnot, that could be me. If the team just needs somebody to execute on it, that could be me as well. [00:39:50] S1: So the advice I'm hearing for people in design that are especially managers, is you almost need to move back into IC in order to truly understand what is happening and how much it's changing, so that you can be a better manager. [00:40:03] S0: I think so. And I think traditionally, at least what I've seen, a lot of the engineering disciplines, when they hire EMs or even sometimes directors there, they actually make the EMs take a rotation for a few months and pick up a few tasks, and really understand how the technology works before they become a full-time manager. And I think design probably needs to do something similar too, where I think in the past design has been much more people management oriented. [00:40:31] S1: What did you find yourself most rusty in when you went back to IC designer? [00:40:35] S0: Actually doing crits, and just really- [00:40:35] S1: Getting criticized.
00:40:35 · Lenny Rachitsky, Jenny Wen
[00:40:35] S1: Getting criticized. [00:40:40] S0: ... Yeah, getting criticized. You're like, oh yeah, it is hard to get critical feedback and to hear it, and to hear it on such a regular basis, because that's the thing you have to do as a designer, is it's a pretty vulnerable exercise to share work and present it with your team, and then also just get a lot of critical feedback and take that all the time. Yeah. [00:41:02] S1: So currently you're leading design/IC designing on cowork. Is that right? [00:41:07] S0: Yeah. [00:41:08] S1: Awesome. So Boris, he was on the pod recently, talked about how there's a lot of debate about what cowork should be, and there's all these big ideas and he's like, "In the end, let's just make it like a terminal, basically, in the product, and just kind of a fancy terminal." Is there anything you could share about just the process of landing on where you landed for that experience of cowork? I have it here on my monitor, by the way, looking at it. [00:41:29] S0: With Cowork specifically, we have had a bunch of different prototypes internally of what that could look like. And it's one of those things where we tried a lot of things, and then I think we weren't really sure when it was actually going to be ready to ship. And then it was sort of everything all at once. We were like, "Okay, we're going to ship it soon." [00:41:53] S1: I think it was 10 days, 10 days of building.
00:41:53 · Lenny Rachitsky, Jenny Wen
[00:41:53] S1: I think it was 10 days, 10 days of building. [00:41:53] S0: Yeah, it was definitely longer than that overall. It was 10 days to get it from what we had internally to something that we were ready to ship externally. So we'd been building it for a while, but we weren't really sure about the actual form it was going to take. And so the way it got there is actually, there was a lot of different other explorations that we had internally on top of different agent harnesses and whatnot. And we just had prototyped little parts of the different interactions that ended up in cowork. So things like when Claude gives you a to do list, we tried a bunch of different form factors for that. We tried a bunch of different form factors for the way it presents you different multiple choice questions. We tried a bunch of different ways to teach people what the use cases are and whatnot. And I don't know if we landed on the best form factor ever, but essentially it was stuff that was already working internally that people liked, that we just thought we were going to get some more signal on by releasing it. So I think forcing ourselves to release it within that 10 days that we did, it was just sort of like, whatever we had, let's put it out there and then let's go out there and iterate from there, which is what we're doing. [00:43:02] S1: And it blew up the internet when you launched it, so it worked out. [00:43:05] S0: Yeah. [00:43:06] S1: Is there a feature of Cowork today that you're either most proud of, or just can't wait to fix and improve?
00:43:06 · Lenny Rachitsky, Jenny Wen
[00:43:06] S1: Is there a feature of Cowork today that you're either most proud of, or just can't wait to fix and improve? [00:43:13] S0: Honestly, I think I'm just most proud of us actually just shipping it, to be honest, and putting it out there. And yeah, I don't know if there's one specific thing yet, because I think when you work on something and you work at so long, especially as a designer, you're like, I don't know. All I can do is see flaws in it, but I think there's a lot of stuff that I'm excited about. We have been iterating, especially on the homepage, and to make that something where it feels more like, "Hey, these are tasks you can give Claude and the tasks that Claude are working on. " And so that actually should be rolling out. It might already be rolled out by the time this comes out. [00:43:54] S1: I see this little randomizer thing, where you click it and gives you all these different ideas. [00:43:58] S0: Yeah, yeah. And then so when you actually start to work with Claude on stuff, it feels more like a to do list. It feels more like these are things Claude's working on, these are things that Claude needs your attention on. And I think there's an opportunity here to make it feel much more like this shared to do list between you and Claude. So excited to iterate on that. And then I'm also excited to think more about what is the actual true form factor of this? Is it stuck in this screen always, or how does this reach out to the different surfaces that it's working with?
00:43:58 · Jenny Wen, Lenny Rachitsky
[00:43:58] S0: Yeah, yeah. And then so when you actually start to work with Claude on stuff, it feels more like a to do list. It feels more like these are things Claude's working on, these are things that Claude needs your attention on. And I think there's an opportunity here to make it feel much more like this shared to do list between you and Claude. So excited to iterate on that. And then I'm also excited to think more about what is the actual true form factor of this? Is it stuck in this screen always, or how does this reach out to the different surfaces that it's working with? [00:44:31] S1: I love that you shared that it wasn't just 10 days to do this thing. There's these numbers that people throw out there, "We built it in 10 days." And your point is there was time spent thinking about what direction it should go, and prototyping, mocking, trying stuff. And then it's like, okay, now we know what we want it to be. Let's build it and ship it.
00:44:31 · Lenny Rachitsky, Jenny Wen
[00:44:31] S1: I love that you shared that it wasn't just 10 days to do this thing. There's these numbers that people throw out there, "We built it in 10 days." And your point is there was time spent thinking about what direction it should go, and prototyping, mocking, trying stuff. And then it's like, okay, now we know what we want it to be. Let's build it and ship it. [00:44:48] S0: Yeah. I think for some reason that became the viral thing that got taken away from all of the cowork announcements, is that it only took 10 days, but I think there have just been so many different explorations, and people that have worked on different pieces of cowork, that it was not just 10 days, and there was a lot of different people involved. It's one of those things where it's like the idea kept coming back, and it's never the right moment or there's different variations of it, and then all of a sudden it's the right moment and it feels like, oh, so obvious all along, but there was a long, long journey to get there. [00:45:24] S1: And by the way, for people that don't know much about cowork, the way I think about it, it's like Claude with hands, or to do stuff on your computer. How would you describe it, just in a sentence or two?